CA2941363A1 - Catalyseurs a base de cyanure bimetallique hautement actifs et procede de production - Google Patents
Catalyseurs a base de cyanure bimetallique hautement actifs et procede de production Download PDFInfo
- Publication number
- CA2941363A1 CA2941363A1 CA2941363A CA2941363A CA2941363A1 CA 2941363 A1 CA2941363 A1 CA 2941363A1 CA 2941363 A CA2941363 A CA 2941363A CA 2941363 A CA2941363 A CA 2941363A CA 2941363 A1 CA2941363 A1 CA 2941363A1
- Authority
- CA
- Canada
- Prior art keywords
- formula
- component
- iii
- polyether
- metal cyanide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 113
- 238000000034 method Methods 0.000 title claims abstract description 30
- 229910052751 metal Inorganic materials 0.000 title claims description 70
- 239000002184 metal Substances 0.000 title claims description 70
- 238000002360 preparation method Methods 0.000 title claims description 21
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 title description 5
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- 229920000570 polyether Polymers 0.000 claims description 126
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 106
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 72
- -1 siloxanes Chemical class 0.000 claims description 57
- 150000002825 nitriles Chemical class 0.000 claims description 41
- 238000006243 chemical reaction Methods 0.000 claims description 32
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 20
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 20
- 239000003446 ligand Substances 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- SZAVHWMCBDFDCM-KTTJZPQESA-N cobalt-60(3+);hexacyanide Chemical compound [60Co+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] SZAVHWMCBDFDCM-KTTJZPQESA-N 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 12
- 229940074391 gallic acid Drugs 0.000 claims description 12
- 235000004515 gallic acid Nutrition 0.000 claims description 12
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 10
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 claims description 10
- RKBAPHPQTADBIK-UHFFFAOYSA-N cobalt;hexacyanide Chemical compound [Co].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] RKBAPHPQTADBIK-UHFFFAOYSA-N 0.000 claims description 10
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 10
- 239000011701 zinc Substances 0.000 claims description 10
- 229910052725 zinc Inorganic materials 0.000 claims description 10
- 239000011592 zinc chloride Substances 0.000 claims description 10
- 235000005074 zinc chloride Nutrition 0.000 claims description 10
- 150000002739 metals Chemical class 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 6
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 6
- BFGKITSFLPAWGI-UHFFFAOYSA-N chromium(3+) Chemical compound [Cr+3] BFGKITSFLPAWGI-UHFFFAOYSA-N 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 claims description 5
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 150000002170 ethers Chemical class 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 4
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 4
- 150000007942 carboxylates Chemical class 0.000 claims description 4
- 150000001913 cyanates Chemical class 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 150000004679 hydroxides Chemical class 0.000 claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 4
- 150000002513 isocyanates Chemical class 0.000 claims description 4
- 150000002540 isothiocyanates Chemical class 0.000 claims description 4
- 150000002823 nitrates Chemical class 0.000 claims description 4
- 150000003901 oxalic acid esters Chemical class 0.000 claims description 4
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 4
- AWDBHOZBRXWRKS-UHFFFAOYSA-N tetrapotassium;iron(6+);hexacyanide Chemical compound [K+].[K+].[K+].[K+].[Fe+6].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] AWDBHOZBRXWRKS-UHFFFAOYSA-N 0.000 claims description 4
- 150000003567 thiocyanates Chemical class 0.000 claims description 4
- YJUIKPXYIJCUQP-UHFFFAOYSA-N trizinc;iron(3+);dodecacyanide Chemical compound [Fe+3].[Fe+3].[Zn+2].[Zn+2].[Zn+2].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] YJUIKPXYIJCUQP-UHFFFAOYSA-N 0.000 claims description 4
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 claims description 4
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 claims description 4
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 claims description 3
- 229920000858 Cyclodextrin Polymers 0.000 claims description 3
- 229910019142 PO4 Inorganic materials 0.000 claims description 3
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 3
- 150000001299 aldehydes Chemical class 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 235000013877 carbamide Nutrition 0.000 claims description 3
- 229940097362 cyclodextrins Drugs 0.000 claims description 3
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 3
- 229930182470 glycoside Natural products 0.000 claims description 3
- 150000002338 glycosides Chemical class 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 3
- 239000010452 phosphate Substances 0.000 claims description 3
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 claims description 3
- 125000005538 phosphinite group Chemical group 0.000 claims description 3
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 3
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical compound OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 claims description 3
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 3
- 229920000515 polycarbonate Polymers 0.000 claims description 3
- 239000004417 polycarbonate Substances 0.000 claims description 3
- 229920000728 polyester Polymers 0.000 claims description 3
- 229920000642 polymer Polymers 0.000 claims description 3
- 150000005846 sugar alcohols Polymers 0.000 claims description 3
- 150000004763 sulfides Chemical class 0.000 claims description 3
- 150000003672 ureas Chemical class 0.000 claims description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- 229910021575 Iron(II) bromide Inorganic materials 0.000 claims description 2
- 229910021577 Iron(II) chloride Inorganic materials 0.000 claims description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 239000011575 calcium Substances 0.000 claims description 2
- INDBQWVYFLTCFF-UHFFFAOYSA-L cobalt(2+);dithiocyanate Chemical compound [Co+2].[S-]C#N.[S-]C#N INDBQWVYFLTCFF-UHFFFAOYSA-L 0.000 claims description 2
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 claims description 2
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 claims description 2
- GYCHYNMREWYSKH-UHFFFAOYSA-L iron(ii) bromide Chemical compound [Fe+2].[Br-].[Br-] GYCHYNMREWYSKH-UHFFFAOYSA-L 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 claims description 2
- 239000004246 zinc acetate Substances 0.000 claims description 2
- 229940102001 zinc bromide Drugs 0.000 claims description 2
- JDLYKQWJXAQNNS-UHFFFAOYSA-L zinc;dibenzoate Chemical compound [Zn+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 JDLYKQWJXAQNNS-UHFFFAOYSA-L 0.000 claims description 2
- NHXVNEDMKGDNPR-UHFFFAOYSA-N zinc;pentane-2,4-dione Chemical compound [Zn+2].CC(=O)[CH-]C(C)=O.CC(=O)[CH-]C(C)=O NHXVNEDMKGDNPR-UHFFFAOYSA-N 0.000 claims description 2
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 claims 3
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 claims 2
- KBJMLQFLOWQJNF-UHFFFAOYSA-N nickel(ii) nitrate Chemical compound [Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O KBJMLQFLOWQJNF-UHFFFAOYSA-N 0.000 claims 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 2
- 229910021580 Cobalt(II) chloride Inorganic materials 0.000 claims 1
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 claims 1
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 claims 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 claims 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 58
- 239000000243 solution Substances 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 28
- 239000012153 distilled water Substances 0.000 description 24
- 239000000047 product Substances 0.000 description 24
- 230000006698 induction Effects 0.000 description 18
- 229920001451 polypropylene glycol Polymers 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 12
- 239000007858 starting material Substances 0.000 description 11
- 239000007864 aqueous solution Substances 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 239000012065 filter cake Substances 0.000 description 7
- 239000004615 ingredient Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 230000035484 reaction time Effects 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 150000002118 epoxides Chemical class 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 239000011261 inert gas Substances 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 238000005133 29Si NMR spectroscopy Methods 0.000 description 5
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 5
- 239000001110 calcium chloride Substances 0.000 description 5
- 235000011148 calcium chloride Nutrition 0.000 description 5
- 229910001628 calcium chloride Inorganic materials 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000007872 degassing Methods 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 229920005862 polyol Polymers 0.000 description 4
- 150000003077 polyols Chemical class 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 229910018540 Si C Inorganic materials 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- 150000002191 fatty alcohols Chemical class 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 229910010271 silicon carbide Inorganic materials 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- WAEMQWOKJMHJLA-UHFFFAOYSA-N Manganese(2+) Chemical compound [Mn+2] WAEMQWOKJMHJLA-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000007046 ethoxylation reaction Methods 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 230000000397 acetylating effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 238000010936 aqueous wash Methods 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GSOLWAFGMNOBSY-UHFFFAOYSA-N cobalt Chemical compound [Co][Co][Co][Co][Co][Co][Co][Co] GSOLWAFGMNOBSY-UHFFFAOYSA-N 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 238000006459 hydrosilylation reaction Methods 0.000 description 1
- MMIPFLVOWGHZQD-UHFFFAOYSA-N manganese(3+) Chemical compound [Mn+3] MMIPFLVOWGHZQD-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 239000006259 organic additive Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920006294 polydialkylsiloxane Polymers 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2642—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds characterised by the catalyst used
- C08G65/2645—Metals or compounds thereof, e.g. salts
- C08G65/2663—Metal cyanide catalysts, i.e. DMC's
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/1608—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes the ligands containing silicon
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/46—Block-or graft-polymers containing polysiloxane sequences containing polyether sequences
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/05—Alcohols; Metal alcoholates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/315—Compounds containing carbon-to-nitrogen triple bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/10—Block- or graft-copolymers containing polysiloxane sequences
- C08L83/12—Block- or graft-copolymers containing polysiloxane sequences containing polyether sequences
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/10—Polymerisation reactions involving at least dual use catalysts, e.g. for both oligomerisation and polymerisation
- B01J2231/14—Other (co) polymerisation, e.g. of lactides or epoxides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Toxicology (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Inorganic Chemistry (AREA)
- Silicon Polymers (AREA)
- Polyethers (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102014209407.0A DE102014209407A1 (de) | 2014-05-19 | 2014-05-19 | Hoch aktive Doppelmetallcyanid-Katalysatoren und Verfahren zu deren Herstellung |
| DE102014209407.0 | 2014-05-19 | ||
| PCT/EP2015/059120 WO2015176920A1 (fr) | 2014-05-19 | 2015-04-28 | Catalyseurs à base de cyanure bimétallique hautement actifs et procédé de production |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2941363A1 true CA2941363A1 (fr) | 2015-11-26 |
Family
ID=53039407
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2941363A Abandoned CA2941363A1 (fr) | 2014-05-19 | 2015-04-28 | Catalyseurs a base de cyanure bimetallique hautement actifs et procede de production |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US9896541B2 (fr) |
| EP (1) | EP3145978B1 (fr) |
| JP (1) | JP2017518411A (fr) |
| CN (1) | CN106459399A (fr) |
| CA (1) | CA2941363A1 (fr) |
| DE (1) | DE102014209407A1 (fr) |
| WO (1) | WO2015176920A1 (fr) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102014213507A1 (de) | 2014-07-11 | 2016-01-14 | Evonik Degussa Gmbh | Platin enthaltende Zusammensetzung |
| EP3168273B1 (fr) | 2015-11-11 | 2018-05-23 | Evonik Degussa GmbH | Polymere durcissable |
| US10287448B2 (en) | 2016-07-08 | 2019-05-14 | Evonik Degussa Gmbh | Universal pigment preparation |
| EP3272331B1 (fr) | 2016-07-22 | 2018-07-04 | Evonik Degussa GmbH | Procede de production de siloxanes contenant des substituts de glycerine |
| EP3321304B1 (fr) | 2016-11-15 | 2019-06-19 | Evonik Degussa GmbH | Mélanges de siloxanes ramifiés-cycliques de type d/t et leurs produits secondaires |
| EP3401353B1 (fr) | 2017-05-08 | 2021-06-23 | Evonik Operations GmbH | Mélanges de siloxanes ramifiés-cycliques de type d/t et leurs dérivés |
| EP3415548B1 (fr) | 2017-06-13 | 2020-03-25 | Evonik Operations GmbH | Procédé de fabrication de polyéthersiloxanes liés par sic |
| EP3415547B1 (fr) | 2017-06-13 | 2020-03-25 | Evonik Operations GmbH | Procédé de fabrication de polyéthersiloxanes liés par sic |
| EP3438158B1 (fr) * | 2017-08-01 | 2020-11-25 | Evonik Operations GmbH | Production de polyéthersiloxanes par une liaison sioc |
| EP3461864A1 (fr) | 2017-09-28 | 2019-04-03 | Evonik Degussa GmbH | Composition durcissable à base de polysiloxanes |
| EP3467006B1 (fr) | 2017-10-09 | 2022-11-30 | Evonik Operations GmbH | Mélanges de siloxanes ramifiés-cycliques de type d/t et leurs produits secondaires |
| SG11202003038YA (en) | 2017-10-10 | 2020-04-29 | Stepan Co | Polymeric dispersants from aralkylated phenols |
| EP3694904B1 (fr) | 2017-10-10 | 2024-09-11 | Stepan Company | Dispersants polymères à partir d'éther phényle glycidique |
| EP3470475B1 (fr) | 2017-10-13 | 2021-01-27 | Evonik Operations GmbH | Composition durcissable pour revêtements à propriété antiadhésive |
| DE112018004605A5 (de) | 2017-10-17 | 2020-05-28 | Evonik Operations Gmbh | Zinkketoiminatkomplexe als Katalysatoren zur Herstellung von Polyurethanen |
| EP3492513B1 (fr) | 2017-11-29 | 2021-11-03 | Evonik Operations GmbH | Procédé de fabrication de polyéthersiloxanes liés au sioc ramifiés dans la partie siloxane |
| EP3524651A1 (fr) | 2018-02-08 | 2019-08-14 | Evonik Degussa GmbH | Dispersion aqueuse de résine polyorganosiloxanhybride |
| EP3611214A1 (fr) | 2018-08-15 | 2020-02-19 | Evonik Operations GmbH | Copolymères bloc polydiméthylsiloxane-polyoxyalkylène linéaires à liaisons sioc |
| EP3611215A1 (fr) | 2018-08-15 | 2020-02-19 | Evonik Operations GmbH | Procédé de production de siloxanes portant des groupes acétoxy |
| EP3663346B1 (fr) | 2018-12-04 | 2023-11-15 | Evonik Operations GmbH | Siloxane réactif |
| CA3132874A1 (fr) | 2019-03-08 | 2020-09-17 | Stepan Company | Tensioactifs reactifs |
| EP3719076A1 (fr) | 2019-04-01 | 2020-10-07 | Evonik Operations GmbH | Dispersion aqueuse de résine polyorganosiloxanhybride |
| EP3744764A1 (fr) | 2019-05-28 | 2020-12-02 | Evonik Operations GmbH | Fabrication de polyéthersiloxanes par une liaison sioc |
| EP3744745A1 (fr) | 2019-05-28 | 2020-12-02 | Evonik Operations GmbH | Fabrication de mousses de polyuréthane |
| EP3744754B1 (fr) | 2019-05-28 | 2024-10-02 | Evonik Operations GmbH | Procédé de production de siloxanes portant des groupes acétoxy |
| EP3744760A1 (fr) | 2019-05-28 | 2020-12-02 | Evonik Operations GmbH | Procédé de fabrication de polyéthersiloxanes liés au sioc ramifiés dans la partie siloxane |
| EP3744774B1 (fr) | 2019-05-28 | 2021-09-01 | Evonik Operations GmbH | Procédé de recyclage des silicones |
| EP3744755B1 (fr) | 2019-05-28 | 2024-10-09 | Evonik Operations GmbH | Procédé de production de siloxanes portant des groupes acétoxy |
| EP3744763B1 (fr) | 2019-05-28 | 2024-08-14 | Evonik Operations GmbH | Polyethérsiloxanes à base de sioc conçus sur mesure |
| EP3744752B1 (fr) | 2019-05-28 | 2024-10-16 | Evonik Operations GmbH | Procédé de fabrication de polysiloxanes à fonction alkoxy non cycliques |
| EP3744759B1 (fr) | 2019-05-28 | 2024-07-17 | Evonik Operations GmbH | Procédé de fabrication de polyéthersiloxanes liés au sioc ramifiés dans la partie siloxane |
| EP3744753B1 (fr) | 2019-05-28 | 2022-04-06 | Evonik Operations GmbH | Procédé de purification d'acétoxysiloxanes |
| EP3744756B1 (fr) | 2019-05-28 | 2024-07-03 | Evonik Operations GmbH | Systèmes acétoxy |
| ES2977903T3 (es) | 2020-03-27 | 2024-09-02 | Evonik Operations Gmbh | Reciclaje de materiales de estructuras planas siliconizadas |
| EP3954740A1 (fr) | 2020-08-14 | 2022-02-16 | Evonik Operations GmbH | Composition antimousse basée sur les polysiloxanes organo-fonctionnels modifiés |
| US11732092B2 (en) | 2020-10-19 | 2023-08-22 | Evonik Operations Gmbh | Upcycling process for processing silicone wastes |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0485637B1 (fr) * | 1990-05-11 | 1997-04-23 | Asahi Glass Company Ltd. | Procede pour produire un compose de polyoxyalkylene |
| US5158922A (en) | 1992-02-04 | 1992-10-27 | Arco Chemical Technology, L.P. | Process for preparing metal cyanide complex catalyst |
| JP3483045B2 (ja) * | 1992-11-30 | 2004-01-06 | 鐘淵化学工業株式会社 | 反応性ケイ素基含有新規重合体およびその製造方法 |
| DE19809539A1 (de) * | 1998-03-05 | 1999-09-09 | Basf Ag | Verfahren zur Herstellung von Doppelmetallcyanidkatalysatoren |
| US6051680A (en) | 1998-06-08 | 2000-04-18 | Arco Chemical Technology, L.P. | Silylated double metal cyanide complex catalysts |
| ATE362951T1 (de) | 1999-02-11 | 2007-06-15 | Bayer Materialscience Ag | Doppelmetallcyanid-katalysatoren für die herstellung von polyetherpolyolen |
| US6613714B2 (en) | 1999-06-02 | 2003-09-02 | Basf Aktiengesellschaft | Multimetal cyanide compounds, their preparation and their use |
| US6800583B2 (en) | 1999-06-02 | 2004-10-05 | Basf Aktiengesellschaft | Suspension of multimetal cyanide compounds, their preparation and their use |
| US6348565B1 (en) | 2000-05-19 | 2002-02-19 | The Dow Chemical Company | Method for preparing metal cyanide catalysts using silane-functional ligands |
| DE10122019A1 (de) | 2001-05-07 | 2002-11-14 | Bayer Ag | Doppelmetallcyanid-Katalysatoren für die Herstellung von Polyetherpolyolen |
| CN1304459C (zh) * | 2002-04-29 | 2007-03-14 | 中国石化集团金陵石油化工有限责任公司 | 一种含硅碳链聚合物的双金属氰化物络合催化剂 |
| DE10228254A1 (de) | 2002-06-24 | 2004-01-22 | Basf Ag | Verfahren zur Herstellung von Polyetheralkoholen |
| CN100368460C (zh) * | 2005-06-17 | 2008-02-13 | 中国科学院过程工程研究所 | 一种双金属氰化物催化剂及其制备方法 |
| DE102008002713A1 (de) | 2008-06-27 | 2009-12-31 | Evonik Goldschmidt Gmbh | Neue Polyethersiloxane enthaltende Alkoxylierungsprodukte durch direkte Alkoxylierung organomodifizierter alpha, omega-Dihydroxysiloxane an Doppelmetallcyanid (DMC)-Katalysatoren, sowie Verfahren zu deren Herstellung |
| DE102008043245A1 (de) * | 2008-10-29 | 2010-05-06 | Evonik Goldschmidt Gmbh | Siliconpolyether-Copolymersysteme sowie Verfahren zu deren Herstellung durch Alkoxylierungsreaktion |
| WO2010063531A1 (fr) * | 2008-12-05 | 2010-06-10 | Evonik Goldschmidt Gmbh | Nouveaux polyéthersiloxanes à groupes alcoxysilyle et leur procédé de production |
| CN103429638B (zh) * | 2010-12-20 | 2016-06-22 | 拜耳知识产权有限责任公司 | 聚醚多元醇的制备方法 |
-
2014
- 2014-05-19 DE DE102014209407.0A patent/DE102014209407A1/de not_active Withdrawn
-
2015
- 2015-04-28 CN CN201580025926.9A patent/CN106459399A/zh active Pending
- 2015-04-28 US US15/312,467 patent/US9896541B2/en not_active Expired - Fee Related
- 2015-04-28 JP JP2016568547A patent/JP2017518411A/ja active Pending
- 2015-04-28 WO PCT/EP2015/059120 patent/WO2015176920A1/fr active Application Filing
- 2015-04-28 EP EP15719679.1A patent/EP3145978B1/fr not_active Not-in-force
- 2015-04-28 CA CA2941363A patent/CA2941363A1/fr not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| WO2015176920A1 (fr) | 2015-11-26 |
| EP3145978A1 (fr) | 2017-03-29 |
| DE102014209407A1 (de) | 2015-11-19 |
| CN106459399A (zh) | 2017-02-22 |
| EP3145978B1 (fr) | 2018-06-27 |
| US9896541B2 (en) | 2018-02-20 |
| US20170088667A1 (en) | 2017-03-30 |
| JP2017518411A (ja) | 2017-07-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US9896541B2 (en) | Highly active double metal cyanide catalysts and method for the production thereof | |
| US10106649B2 (en) | Ethoxylate production using highly active double metal cyanide catalysts | |
| US10662314B2 (en) | Method for producing polyether carbonate polyols | |
| ES2240194T3 (es) | Catalizadores de cianuro bimetalico para la preparacion de polioleteres. | |
| AU716394B2 (en) | Highly active double metal cyanide catalysts | |
| JP6391573B2 (ja) | ポリエーテルカーボネートポリオールの製造方法 | |
| JP6169600B2 (ja) | ポリエーテルエステルカーボネートポリオールの製造方法 | |
| JP5792310B2 (ja) | ポリエーテルカーボネートポリオールの製造方法 | |
| SA516370566B1 (ar) | عملية لتحضير كحولات عديدة الهيدروكسيل لكربونات بولي إيثر | |
| CN103429637A (zh) | 制备具有伯羟基端基的聚醚碳酸酯多元醇的方法和由其制备的聚氨酯聚合物 | |
| RU2346959C2 (ru) | Смесь с активированным инициатором | |
| EP1634644B1 (fr) | Procédé de préparation de catalyseurs à base de cyanures métalliques doubles (catalyseurs DMC) | |
| KR101466803B1 (ko) | 이중금속시안염 촉매 및 이를 제조하는 방법 | |
| CN115135410A (zh) | 制备双金属氰化物催化剂的方法 | |
| KR101342899B1 (ko) | 새로운 유기 착화물제를 이용하여 합성한 이중금속 시안염 촉매 또는 다중금속 시안염 촉매를 이용한 에폭시계 단량체의 개환 중합에 의한 폴리올 제조 | |
| KR101203843B1 (ko) | 새로운 유기 착화물제를 이용하여 합성한 이중금속 시안염 촉매 또는 다중금속 시안염 촉매를 이용한 에폭시계 단량체의 개환 중합에 의한 폴리올 제조 | |
| MXPA02004339A (es) | Catalizadores de cianuro bimetalico para la produccion de polioleteres. | |
| RU2237515C2 (ru) | Двойной металлцианидный катализатор, способ его получения и способ получения полиэфирполиолов | |
| KR100908351B1 (ko) | 랜덤 폴리올 제조용 복금속 시안계 촉매 | |
| MXPA00008727A (en) | Improved double metal cyanide catalysts for producing polyether polyols | |
| KR20110061700A (ko) | 새로운 다관능계 화합물을 단독 착화물제로 이용하여 합성한 이중금속 시안염 촉매 또는 다중금속 시안염 촉매 | |
| MXPA01008136A (en) | Double metal cyanide catalysts for producing polyether polyols | |
| MXPA00006212A (en) | Improved double-metal cyanide catalysts for the production of polyether polyols |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20200831 |